She’d wanted the cottage next to her parents’ place in the Rideau Lakes since childhood. Decades later, she finally got it

The buyer: Stevie O’Brien, a 30-year-old civil litigator at McMillan LLP who rents a one-bedroom in Corktown.

The backstory: O’Brien had long dreamed of owning the vacant place next door to her family cottage on Newboro Lake, north of Kingston. The couple from two properties over were privacy fanatics and had bought it as a buffer from neighbours. As a kid, O’Brien would peek in at the Brady Bunch decor—­avocado-coloured furniture and candy-pink appliances. Even when the owners, who lived in Pennsylvania, stopped visiting the lake in the mid-2000s, they hung on to their properties, hoping their two sons would want them—but the sons weren’t keen on the eight-hour drive.

The buy: When word got out that the ­owners were finally thinking of selling, O’Brien pounced. “I don’t own a house or a car, or have kids yet,” she says, “but cottages only go on the market once a generation.” She called the owners and offered them $250,000, which they took without any back-and-forth. When O’Brien finally crossed the threshold, it was like stepping into a museum: there were vintage board games on the shelves, dishes in the ­cupboard, even an open book on the coffee table. Though she put in a new septic tank and a new roof, she kept most of the throwback ­furniture—including the pink fridge.

(Images: Cottage: Hudson Hayden; O’Brien: Erin Leydon)

Toronto expats find a Canadian home base on the shores of Lake Simcoe

The buyers: Steve Weinberger, the 62-year-old CFO of snack manufacturer Inventure Foods, and his 60-year-old wife, Paula, a freelance executive recruiter. They sold their midtown house eight years ago and moved to Scottsdale, Arizona, for Steve’s job.

The backstory: The Weinbergers wanted to spend more time with their adult children in Canada and figured buying a cottage in Ontario would help. In September, they set a budget of $1 ­million and began the hunt, focusing on Lake Simcoe. Paula immediately fell in love with the photos of a newly renovated four-bedroom, but its ­$1.38-million price tag got a flat no from Steve.

The buy: On her first scouting trip, Paula was repelled by the McMansions masquerading as cottages and concluded that most of Lake Simcoe’s ­offerings weren’t worth a second look—except for the place Steve had vetoed. It was even better in person, with a wall of windows and a saltwater pool. When Steve joined her, she took him there first, knowing everything else would pale in comparison. The ploy worked: he agreed to an offer of $1.1 ­million. After a week and a half of haggling, the Weinbergers upped their offer to $1.27 million with a four-month closing (Steve didn’t want to carry the property over the winter). In April, Paula finally got her dream cottage.

(Images: Cottage: Hudson Hayden; O’Brien: Erin Leydon)

Two Parkdale renters pick the Bruce Peninsula for their first real estate purchase

The buyers: Keith Baguley, a 34-year-old VP of consumer engagement at BT/A Advertising, and his partner, Derek Cameron, a 41-year-old sponsorship advertising manager at a national bank. They live in a rental apartment in Parkdale with their pet Doberman, Venus.

The backstory: Cameron and Baguley weren’t particularly interested in owning property in Toronto, but they were ready to take the plunge on a cottage. They started looking in the Bruce ­Peninsula with a firm $250,000 limit—and soon realized a waterfront lot was out of reach. They focused instead on rustic places within walking distance of a lake.

The buy: After 16 viewings, they found a 125-year-old farmhouse that had been foreclosed two years prior. The lot was a seven-minute stroll from Berford Lake, and, though there was a long to-do list, the $129,000 asking price would keep them well under budget. The property shared a well and driveway, and had a dirt-floor ­basement—all of which repelled traditional lenders. Unable to secure funding, Cameron and Baguley took a break from the hunt, during which the house was pulled off the ­market. As they restarted the search in December, the place was relisted at $99,000. Armed with a loan from Derek’s parents, they offered $9,000 under asking, which was quickly accepted.

A pair of Etobicokers endure a five-year search before buying on Horseshoe Lake

The buyers: Steve Day, the 45-year-old general manager of Paga Technologies, a generator business, and his wife, Fedra, the 41-year-old owner of the furniture store Palazzetti. They live in ­Etobicoke with their sons, ages 10 and 12.

The backstory: Six years ago, the Days were close to paying off their city mortgage, and they decided they could afford a vacation home. Early in the hunt, they asked if Steve’s mom was willing to sell the family cottage on Horseshoe Lake. She was, and the three agreed that Fedra and Steve would pay to fix its crumbling foundation before settling on a fair price. After $80,000 in repairs, the cottage was stable as ever, but Grandma Day had changed her mind. She reimbursed them for the renos and kept the property, forcing the Days to reboot their search.

The buy: The options within their $350,000 budget were either swampy and dark, or dilapidated. Rather than take on another reno, they upped their ceiling by $100,000. Even still, it took five years to find the one. In February 2013, they got a tip about a potential prospect—a modest cottage on a lot that sloped right down to the lake. “The bedrooms were tiny, but who cares?” says Fedra. “The whole point of a cottage is us not being in it.” The sellers were asking $475,000, but the Days talked them down by $17,000. The papers were signed without agents within a week.

(Image of Days: Erin Leydon)

A couple calls off the hunt—and the perfect Muskoka pad falls into their laps

The buyers: Anita Walters, a 60-year-old co-manager of an orphanage in Kikima, Kenya, with her husband, Eric, a 57-year-old YA author. They live in Mississauga.

The backstory: With retirement approaching, Anita and Eric started looking in earnest for a Muskoka cottage. On their checklist: western exposure, year-round access, proximity to the water and space for the whole ­family—four grown children, spouses and the crush of grandchildren who are, Anita hopes, on their way. They saw 20 places over two years with no luck.

The buy: They were taking a winter breather from the search when they got a tip from Anita’s university roommate, who had hosted the couple at her ­Stewart Lake cottage for years: a neighbour wanted to sell privately. Though the place was covered in snow when they visited, Anita and Eric offered $15,000 under asking, and the sellers bit. In the end, says Anita, “We didn’t find the cottage. The cottage found us.”